Tetrahydrofuran → 1-Trichlorosilylpyrene

HRID 1472932Notes

Reaction equation

[Li]CCCC.Br[C:7]1[C:20]2[C:21]3=[C:22]4[C:17](=[CH:18][CH:19]=2)[CH:16]=[CH:15][CH:14]=[C:13]4[CH:12]=[CH:11][C:10]3=[CH:9][CH:8]=1.C1COCC1.[Si:28](Cl)([Cl:31])([Cl:30])[Cl:29]>C1COCC1.CCOCC>[Cl:29][Si:28]([Cl:31])([Cl:30])[C:7]1[C:20]2[C:21]3=[C:22]4[C:17](=[CH:18][CH:19]=2)[CH:16]=[CH:15][CH:14]=[C:13]4[CH:12]=[CH:11][C:10]3=[CH:9][CH:8]=1

Participants

Conditions

Temperature: -60 °C

Procedure

Under a dry nitrogen atmosphere, n-BuLi (10.6 mL, 1.6 M) in hexanes was added drop-wise to a cooled (−60° C.) solution of 1-bromopyrene (5.01 g, 0.018 mol) in THF/Et2O (1:1) (80 mL) and stirred for 2 hours at −60° C. The solution was cooled to −90° C. and a THF solution of SiCl4 (8.66 g, 0.051 mol) (10 mL) was added slowly and stirred for 24 hours at room temperature. The reaction mixture was evaporated to dryness, washed in Et2O (100 mL), and filtered to remove any unreacted 1-bromopyrene and LiBr. The filtrate was collected and evaporated to dryness to give a 48% yield of 1-trichlorosilylpyrene, a yellow powder. 1HNMR (CDCl3, ppm) 8.66 (d, J=9.3 Hz, 1H), 8.59 (d, J=8.1 Hz, 1H), 8.30 (m, 5H), 8.11 (m, 2H). 13C{1H} NMR (CDCl3, ppm) 136.18 (C), 135.85 (C), 133.13 (CH), 132.06 (C), 131.30 (C), 131.22 (CH), 130.31 (CH), 127.96 (CH), 127.67 (CH), 127.61 (CH), 126.65 (CH), 125.61 (C), 125.01 (CH), and 124.39 (C). 29Si{1H} (CDCl3, ppm) −1.64 (s).

Workup

temperatureThe solution was cooled to −90° C.
stirringstirred for 24 hours at room temperature
customThe reaction mixture was evaporated to dryness
washwashed in Et2O (100 mL)
filtrationfiltered
customto remove any unreacted 1-bromopyrene and LiBr
customThe filtrate was collected
customevaporated to dryness

Sources & evidence

ORD record: ord-b896d5ac20f04bce8302835acbc6178c
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012673B1

Reaction notes

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